Dichloromethane → 2-(2,5,8,11-Tetraoxadodecan-1-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxine

HRID 890328Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:7]([O:8][CH3:9])=[CH:6][S:5][CH:4]=1.[CH3:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21]C(O)CO.C(Cl)Cl>C1(C)C=CC=CC=1>[CH3:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH:1]1[O:2][C:3]2=[CH:4][S:5][CH:6]=[C:7]2[O:8][CH2:9]1

Participants

Conditions

Temperature: 100 °C

Procedure

A transetherification reaction between 3,4-dimethoxythiophene (12.9 g, 89 mmol) and {2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxymethyl}-1,2-ethanediol (24.5 g) in toluene (150 mL) was performed by heating (at 100° C.) a mixture of these compounds under a continuous nitrogen flow for 24 h. Subsequently, the reaction mixture was poured into methylene chloride (200 mL) and the organic phase was washed with a 1M aqueous sodium hydrogen carbonate solution, an aqueous concentrated sodium chloride solution, dried with anhydrous magnesium sulphate and concentrated. This resulted in a viscous oil. Pure 2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxymethyl}-2,3-dihydro-thieno[3,4-b][1,4]dioxine was finally obtained by vacuum distillation.

Workup

additiona mixture of these compounds under a continuous nitrogen flow for 24 h
washthe organic phase was washed with a 1M aqueous sodium hydrogen carbonate solution
dry with materialan aqueous concentrated sodium chloride solution, dried with anhydrous magnesium sulphate
concentrationconcentrated
customThis resulted in a viscous oil

Sources & evidence

ORD record: ord-7112443bd7e843709771edfb89254951
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06995223B2

Reaction notes

Loading…